Grant-Lee Phillips isn't exactly sure how he came to headline Meadow Grass, and says he's never played with any of the other festival performers before. But there's at least one reason why the local stop feels right to him.

"I have an extensive catalog of moon songs, lunar songs," he says with a laugh. "So it's probably high time that I take to the hills."

Though he occasionally covers David Bowie's "Ashes to Ashes," Phillips has always written from the ground, looking up. In the '90s with the semi-eponymous Grant Lee Buffalo, that often meant songs full of 12-string guitar feedback, heavy drum hits, and lyrics conjuring dark imagery of the past two American centuries.

"Mighty Joe Moon," title track to GLB's best-known album, references the Appalachians' Cumberland Gap, while the album evokes tragic figures from Tecumseh to John Wayne Gacy.

Since going solo in 1999, however, he's drawn more and more from his own life; he called 2007's Strangelet his most personal record, and is now doing the same with his newest release, Little Moon. He's singing lyrics like, "I got a little girl a-cutting teeth / A pretty wife who's in the bed / Rather be makin' love or makin' peace / Don't wanna live a life of dread."

"That song ["It Ain't the Same Old Cold War, Harry"] has the most to do with becoming a parent," says Phillips, whose 2-year-old daughter, Violet, has helped develop his appreciation for both smoothies and the music of Yo Gabba Gabba! "And going back to that, you know, like feeling more and more invested in seeing to it that we have a safe, tender world to bring up our children."

The iTunes editors' pick for Best Singer-Songwriter Album of 2009, Little Moon is fueled by a stubborn optimism that Phillips does little to camouflage. The sub-three-minute, drum-thumping opener goes by "Good Morning Happiness," and the animated video he created for it features, in no particular order, a gorilla jauntily vacuuming, Frankenstein descending upon a plate of pancakes, and a footrace between what appears to be a glazed donut and a Devil Dog.

"I've always been a pretty ridiculous person, which I tended to hide away for a long time," Phillips says. "And now I'm just kind of realizing that, you know, all these songs that I would've like, tucked away and put out under someone else's name, maybe it's time to start sharing these things."

And to not look back. Little Moon was recorded in just five days in early May of last year, and by month's end was mixed and mastered. It came out in October, and Phillips has taken the songs to stages in his native California and points east.

Many of those dates have been solo acoustic, whereas at MeadowGrass, he'll be joined by bassist Paul Bryan (who also produced the album) and drummer Sebastian Aymanns. They'll be sans the strings and horns that fill out a couple Little Moon tracks, but the freedom of playing them as a trio — in the open air for the first time — should allow for a looseness befitting a festival atmosphere.

In fact, Phillips jokes that in the limited dates they've had together, they've already seen a couple songs evolve "into free-form jazz."

"Maybe that's not the word," he says, laughing again. "They've been evolving, though."